1. Field of Invention.
The present invention relates to novel fused imidazoheterocyclics which have one substituted imidazo nitrogen and an aryl substitution on the carbon atom between the two imidazo nitrogens, a novel process therefor and novel intermediates in the preparation thereof. The imidazoheterocyclic compounds have CNS activity.
2. Information Disclosure Statement.
The preparation of 2-aryl-substituted imidazo [4,5-b]pyridines has been described by Garmaise, D. L. and Komlossy, J. in J. ORG. CHEM. 29(1) 3403-5 (1964). Unlike the present invention, the compounds have no substitution on the imidazo nitrogen.
Preparation of imidazopyridines having alkylaminoalkyl substitution on one imidazo nitrogen and benzyl substitution on the carbon between the two imidazo nitrogens (position 2) has been described in U.S. Pat. No. 2,987,518. The compounds of the present invention do not have alkylaminoalkyl substitution on an imidazo nitrogen.
2-Phenyl-imidazopyridines have been disclosed in U.S. Pat. Nos. 4,327,100, 4,353,909 and 3,985,891 as cardiotonics and blood pressure altering drugs. In U.S. Pat. No. 3,985,891, one compound is substituted in the 3-position by methyl. The compounds of the present invention are substituted in the 3-position by other radicals.
Benzimidazoles substituted on nitrogen by, for example, N,N-diethylacetamide, and in the two position by an ethoxybenzyl radical, are disclosed in Chemical Abstracts Vol. 66, 65425g.
Benzimidazoles substituted on nitrogen by carboxylic acid ethyl ester and in the two position by a 2-pyridinyl radical are disclosed in J. Med. Chem. 1980, 23(7), 734-8 as having anti-inflammatory activity.
(2-Phenyl-1 benzimidazolyl)propionic acid having growth-stimulating activity in the cotton plant is disclosed in Chemical Abstracts 100, 81244r (1984).
Imidazo[4,5-b]pyridines substituted in the 2-position by ##STR2## have been disclosed in Monatsh. Chem. (1975) 106(5), pp 1059-69 (C.A. 84, 59315u) as having no significant biological activity as compared to 2-(.alpha.-hydroxybenzyl)benzimidazole.
N,N-6-Trimethyl-2-(4-methylphenyl)imidazo[1,2a] pyridine-3-acetamide has been disclosed in NAUNYN-SCHMIEDBERG's ARCH. PHARMACOL (1985), Vol 330, pp 248-251. In contrast to the compounds of the present invention, the compound has a nitrogen shared by both the imidazo moiety and the pyridine moiety and the acetamide radical is on a carbon of the imidazo moiety rather than on an imidazo nitrogen.